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Search results; Over 1,000 homes in Winchester

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Guest favourite
Flat in Winchester
Riverview 2 … enjoy the view !
1 bedroom, 1 bed, 1 private bathroom
1–6 Nov
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4.89 out of 5 average rating, 190 reviews
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Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 bathrooms
18–23 Oct
4.97 out of 5 average rating, 147 reviews
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Home in Winchester
Aisling House - Historic Hospitality
7 bedrooms, 8 beds, 4 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 bathrooms
26–31 Oct
4.96 out of 5 average rating, 104 reviews
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Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 101 reviews
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Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 124 reviews
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Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.92 out of 5 average rating, 230 reviews
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Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.92 out of 5 average rating, 971 reviews
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Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.92 out of 5 average rating, 91 reviews
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Guest favourite
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
4.81 out of 5 average rating, 72 reviews
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Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 bedrooms, 3 queen beds, 3.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 37 reviews
Photo 1 of 29
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.99 out of 5 average rating, 95 reviews
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Guest favourite
Home in Mount Sterling
Five O’clock Somewhere
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
4.88 out of 5 average rating, 41 reviews
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Hotel room in Lexington
Hotel LEX | Courtyard 2 Queen | Indoor Pool
1 bedroom, 2 queen beds, 1 bathroom
1–6 Oct
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Cabin in Clay City
Brand New Cabin - Coming Oct 1st- 15 min to Gorge
2 bedrooms, 1 queen bed, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Farm stay in Mount Sterling
Mount Sterling Horse Farm
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 36 reviews
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Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 197 reviews
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Guest favourite
Cabin in Lexington
1800’s Historical Log Cabin Lexington KY
2 bedrooms, 5 beds, 2.5 bathrooms
7–12 Nov
4.88 out of 5 average rating, 146 reviews